I have a long standing love affair with the United States, having grown up on a regular diet of American TV shows and films as a child in the 1970s and 80s. We have visited a lot as a family, checking off the iconic cities: New York, New Orleans, LA, San Francisco and Chicago. Each is lovable in its own way, but now I have had the chance to plan a visit to Boston, I have been won over. Here are 10 places in Boston that stole my heart.
Our favourite things to do in Boston on a first visit – wander Beacon Hill and Acorn Street, walk the Freedom Trail, eat cannoli in North End, tour the Isabella Stewart Gardner Museum, catch the Red Sox at Fenway Park, shop Newbury Street and stroll the Harborwalk.
We stayed in a boutique hotel on Charles Street in the historic Beacon Hill neighbourhood, named for the signal beacon that once warned inhabitants of danger. Charles Street is a smart row of handsome red brick buildings, boutique shops (books, clothes, leather goods and nuts!) and eateries. In late September the hilly side streets were lined with trees changing colour, and the window displays were tasteful and enticing. Breakfast was never a challenge, with the likes of Cobblestones Cafe and Tatte Bakery full of pastry delights.
While you are here, head to Acorn Street, one of the prettiest streets in Boston: cobblestones, gas lamps and a row of Federal style houses built in the 1820s for artists and tradespeople. Lucky them.
Boston is a city of 23 neighbourhoods, so explore and find your own favourite. North End, Back Bay, Fenway-Kenmore and Charlestown are all worth your time on a first visit.
Walking from Charles Street towards Fenway-Kenmore, we wandered slowly along Beacon Street, taking in the lines of attractive brownstones. Many houses had dressed their stoops with autumn displays of pumpkins in every shade of orange and green, and further along we passed Boston University frat houses proudly displaying their Greek letters. We visited in late September; closer to Halloween, the displays must be even better.
For the most incredible doorstep displays of all, take the 30 minute train from Boston to Salem and pair the pumpkins with Salem's dark history.
Starting from Boston Common, the historic Freedom Trail links the key sites of the American Revolution around the city. We walked it under our own steam with guidebooks and information boards, but guided walks leave from the Visitors Centre, and narrated trolley tours run if your feet need a rest. I am a novice historian and found it fascinating – you can’t help but feel the history seeping in.
Head to the Boston Tea Party Ships and Museum on the waterfront, where you can throw your own crate of tea into Boston Harbor from a replica tea clipper.
North End was settled by Italian immigrants and still feels like a little Italy – streets decorated in red and green, stand up espresso bars and cosy pizzerias. Leave room for dessert at Mike’s Pastry, famous for cannoli. The queue gives you time to face the overwhelming flavour list, and your choice comes boxed in white and blue and tied with string pulled from balls hanging from the ceiling.
The main rivals are Modern Pastry and Bova's Bakery, both nearby. Everyone has their favourite cannoli outlet. Which will be yours?
The Emerald Necklace is an 11 km chain of parks and waterways through Boston, designed by landscape architect Frederick Law Olmsted, taking in the Back Bay Fens, the Riverway, Olmsted Park, Jamaica Pond, the Arnold Arboretum and Franklin Park. We walked shady, tree lined paths through the Back Bay Fens, past the well tended allotments of the Fenway Garden Society and a sports field full of school kids playing baseball. A haven of tranquillity in the city centre, with just the ducks and a few joggers for company.
Boston Common, America's oldest public park, and the Boston Public Garden with its famous swan boats. The green spaces were full of joggers, including a Sunday morning fun run on the Common.
A very special museum in Fenway-Kenmore, once the home of the wealthy Isabella Stewart Gardner, who collected art on her travels for 40 years and wanted people to see it in situ after her death. Her four storey house, built in the style of a Venetian palazzo around a large plant filled courtyard, is itself a work of art, and every inch of wall carries part of a staggering collection of over 2,500 pieces.
Book tickets in advance. Unsurprisingly, it is very popular.
Still hungry for art? The Museum of Fine Arts nearby holds Monet, Gauguin, Rembrandt and Van Gogh masterpieces.
The oldest and most storied baseball ground in the United States, Fenway Park has been home to the Red Sox since 1912. Book a stadium tour, or simply settle into the historic green stands for a game: the atmosphere is great fun and a proper piece of American culture.
Consider a cushion for the Grandstand seats, which date to 1934 and have no padding. All part of the experience..
Bostonians are sport mad. Depending on the season, a Boston Bruins ice hockey game is another cracking night out.
Back Bay was reclaimed from swampy land and is now one of Boston’s most affluent areas, with Newbury Street running through the middle – a wide avenue of designer boutiques and restaurants, great for window shopping. Stop at Stephanie’s on Newbury, grab a patio seat and build a bespoke Bloody Mary from their menu. I recommend adding bacon and jalapenos.
Shopped out? The famous Boston Public Library on Copley Square is around the corner. You may have seen it in the movies.
I do love a city on the water, and Boston has the Charles River on one side and Massachusetts Bay on the other. We strolled the Harborwalk from Christopher Columbus Waterfront Park to the Boston Tea Party Ships and Museum, passing Long Wharf, small marinas and boats of every size, and watching planes drop into Boston Logan just across the water, strangely close to the city.
To get out on the water, ferries run to the Boston Harbor Islands, and whale watching trips sail in season.
Cross to Charlestown for the USS Constitution and the Navy Yard, then climb to the Bunker Hill Monument, the official end of the Freedom Trail.
Boston sits at the heart of New England and is the perfect base for exploring beyond Massachusetts: Maine to the northeast, New Hampshire to the north, Vermont to the northwest, and Rhode Island and Connecticut to the south.
In our attempt to visit all six New England states, we split the region into two trips: a loop from Long Island through Connecticut and Rhode Island into western Massachusetts, and a loop from Boston through Southern Maine, New Hampshire and Vermont.
Boston is one of the closest US destinations to the UK, 7 to 8 hours out and faster home with the Gulf Stream behind you.
In closing
We spent 3 days in Boston before the road trip, and I would happily have stayed longer.
Smart, attractive, interesting, and it felt safe and comfortable throughout. Here's to the next time!
Enjoy your travels!
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